1-Azido-N'-(phenylsulfonyl)methan-imid-amide.

In the title compound, C(7)H(7)N(5)O(2)S, the aromatic ring is oriented at dihedral angles of 79.46 (2) and 89.17 (2)°, respectively, with respect to the amino-(azido)-methyl and the S(6) six-membered ring motif generated by an intra-molecular N-H⋯O inter-action [N⋯O = 2.8901 (15) Å]. Inter-molecular N-H⋯O hydrogen bonds [N⋯O = 2.9177 (15) and 2.9757 (15) Å] generate an infinite one-dimensional network along the base vector (010).

Related literature

For the synthesis, see: Mahmood et al. (2011 ▶). For related structures, see: Denny et al. (1980 ▶); Mahmood et al. (2011 ▶); Müller & Bärnighausen (1970 ▶). For graph-set notations, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C7H7N5O2S

M = 225.24

Triclinic,

a = 7.0399 (2) Å

b = 7.1714 (2) Å

c = 10.3670 (3) Å

α = 90.267 (1)°

β = 98.997 (1)°

γ = 110.358 (1)°

V = 483.67 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.32 mm−1

T = 296 K

0.35 × 0.31 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.896, T max = 0.962

8598 measured reflections

2422 independent reflections

2246 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.097

S = 1.06

2422 reflections

143 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811037718/pv2447sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037718/pv2447Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811037718/pv2447Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C7H7N5O2S	Z = 2
Mr = 225.24	F(000) = 232
Triclinic, P1	Dx = 1.547 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.0399 (2) Å	Cell parameters from 6153 reflections
b = 7.1714 (2) Å	θ = 3.0–28.5°
c = 10.3670 (3) Å	µ = 0.32 mm−1
α = 90.267 (1)°	T = 296 K
β = 98.997 (1)°	Plate, colourless
γ = 110.358 (1)°	0.35 × 0.31 × 0.12 mm
V = 483.67 (2) Å3

Bruker APEXII CCD diffractometer	2422 independent reflections
Radiation source: fine-focus sealed tube	2246 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 28.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→9
Tmin = 0.896, Tmax = 0.962	k = −9→9
8598 measured reflections	l = −13→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.059P)2 + 0.1064P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2422 reflections	Δρmax = 0.30 e Å−3
143 parameters	Δρmin = −0.30 e Å−3
3 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.178 (13)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
S1	0.29872 (4)	0.66106 (4)	0.14334 (3)	0.03096 (13)
O1	0.22775 (17)	0.82450 (15)	0.15249 (12)	0.0501 (3)
O2	0.37880 (15)	0.63793 (15)	0.02689 (9)	0.0407 (2)
N4	−0.18866 (18)	0.17258 (17)	0.21333 (12)	0.0412 (3)
N3	−0.05785 (18)	0.12367 (17)	0.16650 (12)	0.0406 (3)
C7	0.10971 (19)	0.28677 (17)	0.14142 (11)	0.0297 (2)
N1	0.11035 (16)	0.46635 (15)	0.16629 (10)	0.0318 (2)
N2	0.24609 (19)	0.22835 (17)	0.09706 (13)	0.0405 (3)
H2N	0.346 (2)	0.310 (2)	0.0691 (19)	0.061*
H1N	0.230 (3)	0.1058 (15)	0.096 (2)	0.061*
N5	−0.3157 (2)	0.1915 (2)	0.25610 (18)	0.0632 (4)
C1	0.49613 (19)	0.69027 (18)	0.27813 (12)	0.0317 (3)
C2	0.6735 (2)	0.6594 (2)	0.26000 (14)	0.0415 (3)
H2	0.6882	0.6209	0.1775	0.050*
C3	0.8287 (3)	0.6865 (3)	0.36578 (18)	0.0598 (5)
H3	0.9484	0.6653	0.3549	0.072*
C4	0.8055 (3)	0.7449 (3)	0.48716 (18)	0.0676 (5)
H4	0.9109	0.7641	0.5579	0.081*
C6	0.4725 (3)	0.7480 (3)	0.40091 (15)	0.0498 (4)
H6	0.3525	0.7680	0.4125	0.060*
C5	0.6289 (3)	0.7752 (3)	0.50550 (17)	0.0650 (5)
H5	0.6150	0.8141	0.5882	0.078*

	U11	U22	U33	U12	U13	U23
S1	0.03183 (19)	0.02277 (18)	0.04005 (19)	0.01043 (12)	0.00916 (12)	0.00792 (11)
O1	0.0508 (6)	0.0279 (5)	0.0787 (8)	0.0209 (5)	0.0146 (5)	0.0126 (5)
O2	0.0400 (5)	0.0447 (6)	0.0364 (5)	0.0115 (4)	0.0113 (4)	0.0105 (4)
N4	0.0348 (6)	0.0323 (6)	0.0514 (7)	0.0040 (5)	0.0105 (5)	0.0104 (5)
N3	0.0391 (6)	0.0269 (5)	0.0526 (7)	0.0052 (5)	0.0138 (5)	0.0038 (5)
C7	0.0306 (6)	0.0250 (5)	0.0314 (5)	0.0078 (4)	0.0040 (4)	0.0044 (4)
N1	0.0294 (5)	0.0253 (5)	0.0416 (5)	0.0092 (4)	0.0095 (4)	0.0040 (4)
N2	0.0444 (7)	0.0260 (5)	0.0560 (7)	0.0136 (5)	0.0194 (5)	0.0053 (5)
N5	0.0470 (8)	0.0558 (9)	0.0908 (11)	0.0143 (7)	0.0320 (8)	0.0185 (8)
C1	0.0327 (6)	0.0232 (5)	0.0370 (6)	0.0058 (4)	0.0086 (5)	0.0025 (4)
C2	0.0364 (7)	0.0482 (8)	0.0397 (6)	0.0144 (6)	0.0074 (5)	−0.0006 (6)
C3	0.0377 (8)	0.0830 (13)	0.0552 (9)	0.0204 (8)	0.0000 (7)	0.0004 (9)
C4	0.0518 (10)	0.0894 (15)	0.0448 (8)	0.0108 (10)	−0.0068 (7)	−0.0014 (8)
C6	0.0487 (8)	0.0557 (9)	0.0453 (8)	0.0155 (7)	0.0158 (6)	−0.0042 (7)
C5	0.0696 (12)	0.0791 (13)	0.0376 (7)	0.0152 (10)	0.0099 (8)	−0.0089 (8)

S1—O1	1.4330 (10)	C1—C2	1.3811 (19)
S1—O2	1.4419 (10)	C1—C6	1.3885 (18)
S1—N1	1.6057 (11)	C2—C3	1.382 (2)
S1—C1	1.7650 (13)	C2—H2	0.9300
N4—N5	1.1055 (19)	C3—C4	1.376 (3)
N4—N3	1.2529 (17)	C3—H3	0.9300
N3—C7	1.4022 (16)	C4—C5	1.375 (3)
C7—N1	1.3105 (15)	C4—H4	0.9300
C7—N2	1.3134 (16)	C6—C5	1.379 (3)
N2—H2N	0.837 (9)	C6—H6	0.9300
N2—H1N	0.846 (9)	C5—H5	0.9300
O1—S1—O2	117.23 (7)	C6—C1—S1	119.38 (11)
O1—S1—N1	105.53 (6)	C1—C2—C3	119.31 (14)
O2—S1—N1	112.47 (6)	C1—C2—H2	120.3
O1—S1—C1	107.62 (7)	C3—C2—H2	120.3
O2—S1—C1	107.32 (6)	C4—C3—C2	119.78 (16)
N1—S1—C1	106.07 (6)	C4—C3—H3	120.1
N5—N4—N3	171.37 (15)	C2—C3—H3	120.1
N4—N3—C7	113.51 (11)	C5—C4—C3	121.01 (17)
N1—C7—N2	130.53 (12)	C5—C4—H4	119.5
N1—C7—N3	118.15 (11)	C3—C4—H4	119.5
N2—C7—N3	111.31 (11)	C5—C6—C1	119.30 (15)
C7—N1—S1	121.29 (9)	C5—C6—H6	120.4
C7—N2—H2N	120.8 (13)	C1—C6—H6	120.4
C7—N2—H1N	118.7 (13)	C4—C5—C6	119.79 (16)
H2N—N2—H1N	120.5 (18)	C4—C5—H5	120.1
C2—C1—C6	120.81 (13)	C6—C5—H5	120.1
C2—C1—S1	119.80 (10)
N4—N3—C7—N1	−1.19 (18)	O2—S1—C1—C6	169.50 (11)
N4—N3—C7—N2	177.67 (12)	N1—S1—C1—C6	−70.08 (12)
N2—C7—N1—S1	0.0 (2)	C6—C1—C2—C3	0.0 (2)
N3—C7—N1—S1	178.63 (9)	S1—C1—C2—C3	178.76 (13)
O1—S1—N1—C7	167.67 (11)	C1—C2—C3—C4	−0.5 (3)
O2—S1—N1—C7	38.71 (12)	C2—C3—C4—C5	0.6 (3)
C1—S1—N1—C7	−78.31 (11)	C2—C1—C6—C5	0.2 (2)
O1—S1—C1—C2	−136.24 (12)	S1—C1—C6—C5	−178.49 (14)
O2—S1—C1—C2	−9.24 (13)	C3—C4—C5—C6	−0.3 (4)
N1—S1—C1—C2	111.19 (12)	C1—C6—C5—C4	−0.1 (3)
O1—S1—C1—C6	42.49 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N···O1i	0.85 (1)	2.10 (1)	2.9177 (15)	163.(2)
N2—H2N···O2ii	0.84 (1)	2.23 (1)	2.9757 (15)	148.(2)
N2—H2N···O2	0.84 (1)	2.33 (2)	2.8901 (15)	125.(2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N⋯O1i	0.85 (1)	2.10 (1)	2.9177 (15)	163 (2)
N2—H2N⋯O2ii	0.84 (1)	2.23 (1)	2.9757 (15)	148 (2)
N2—H2N⋯O2	0.84 (1)	2.33 (2)	2.8901 (15)	125 (2)

Symmetry codes: (i) ; (ii) .